Teaching Don Quijote de la Mancha in translation is an enterprise fraught with perils. Texts read in translation should afford what Venuti calls “an illusion of transparency”, yet, more often than not, the translator crops up in the most unexpected places obscuring the author’s intention and domesticating the text to the point that it becomes almost unrecognizable. Although a good translator strives to “acculturate” the reader with pointed cues designed to ease the passage through the narrative, sometimes this effect is difficult to achieve. In a text as seemingly impenetrate and intricate as Don Quijote de la Mancha, this task becomes even harder. Among some of the challenges this seminal work presents are translation issues (both internal and external), the complexity of the narrative structure and cultural differences which need to be addressed, particularly when teaching the text to English speaking students. In this essay I examine Cervantes’ masterpiece under this light, focusing on the aspects mentioned above. My intention in this essay is to highlight the challenges teaching Don Quijote in translation presents as well as to examine the work of four different translators I have used in the past. I hope my work helps both scholars and teachers while also enhancing their experience reading and studying Don Quijote de la Mancha.